Thionyl Chloride → HCID 59717988, compound

HRID 1726511Notes

Reaction equation

HRID 1726511 reaction equation
[C:1]([NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[C:15]2[S:20]([OH:23])(=O)=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>ClCCl>[C:1]([NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[C:15]2[S:20]([Cl:26])(=[O:23])=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6611518HCID 6611518, compound

Product 1

HCID 59717988HCID 59717988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 5-benzoylamino-napthalene-1-sulfonic acid (1.5 g, 3.51 mmol) in dichloromethane (5 ml), was added thionyl chloride (0.359 ml, 4.92 mmol). The resultant solution was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was quenched by pouring into ice water and extracting with ethyl acetate. The organic extracts were washed with brine, dried over MgSO4 and concentrated to provide the crude intermediate 44 as a yellow oil that was used without further purification.

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into ice water
  3. extractionextracting with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-72461c549cb442ada7ef70f151a20d10
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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